


(If I try) can I win you over?

by jensenacklesruinedmylife



Category: Supernatural
Genre: Angst and Humor, Cas is flirty, Cas learns how to flirt, Castiel/Dean Winchester First Kiss, Dean is an idiot but we love him, First Kiss, Flirting, Fluff and Angst, Idiots in Love, Love Confessions, M/M, Romance, Rowena ships destiel, dean is flustered, nothing a little magic can't fix
Language: English
Status: Completed
Published: 2020-09-18
Updated: 2020-09-18
Packaged: 2021-03-07 22:00:11
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,257
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26524849
Author URL: https://archiveofourown.org/users/jensenacklesruinedmylife/pseuds/jensenacklesruinedmylife
Summary: Written forClaraon tumblr!Cas doesn't know how to show Dean his affection.Rowena gives him a little help in the flirtation department.Dean is, of course, confused andveryflustered.
Relationships: Castiel/Dean Winchester
Comments: 18
Kudos: 251





	(If I try) can I win you over?

It starts after they work a case with Rowena, which, in hindsight, should have been Dean’s first clue. 

Rowena convinces Cas to stay behind for a while, says she has a _gift_ for him. Dean, of course, says _hell no,_ but Cas assures him that it’s fine. They may work with Rowena from time to time, but Dean doesn’t trust the witch as far and he can throw her. He threatens Rowena anyway, and she dramatically promises that she won’t harm a hair on Cas’s head. Satisfied, Dean leaves with Sam and Jack in tow, fully intending on burning Rowena alive if Cas comes back harmed in any way. 

Cas shows up a couple hours after the rest of them get back to the bunker, _poofing_ into the kitchen with a flap of his wings. Dean’s sharing a beer with Sam when his head snaps up at the sound. 

“Hey,” he says, giving the angel a once over, “You good?”

“I am,” Cas nods, then smiles, “Very good, actually.”

“Very?” Sam chuckles, “What did Rowena want with you?”

“She wanted to talk.”

Sam raises an eyebrow. “Talk?”

“Yes, to help me with a little problem I’ve had. She gave me some… advice,” he smiles.

Dean’s still suspicious. “You sure she didn’t hurt you? Because if she did, I swear to God –.”

“Dean, I’m okay, I promise,” Cas answers calmly.

Dean gives Cas a doubtful look, but the angel just stands there smiling, and finally Dean sighs.

“Fine, if you say so. You want a drink? There’s more in the fridge.”

Cas looks like he’s going to say yes, but then he pauses and shakes his head. “I think I’ll head to the library, actually. You two enjoy.”

With that, he walks out of the kitchen, glancing over his shoulder at Dean before turning the corner.

“What’s with him?” Dean asks, taking a sip of his beer.

“Heck if I know,” Sam shrugs, “Just being his weird angel self, I guess.”

They sit in the kitchen talking for another half hour before Sam, the princess that he is, calls it a night. Dean’s heading to his own bedroom when he feels a strange pull and decides to see if the angel is still in the library. Not that he _needs_ to see him or anything, he just wants to check on him, that’s all.

Sure enough, Cas is sitting in one of the fancy library chairs reading an old book. He sits with his legs crossed, leaning on the arm of the chair as he flips a page, blue eyes shining even in the lowlight of the room. His trench coat lays over the back of the chair, and his tie is loose around his neck. For a second, Dean forgets he’s an Angel of the Lord, and sees his best friend, someone he cares about, safe and relaxed in their home.

 _Wait, what?_ Dean shakes his head. _When did I get so lame?_

“Dean?” Cas looks up from his book, “Shouldn’t you be in bed?” 

“What are you, my mom?” Dean scoffs, walking further into the room, “Just uh, wanted to check on you, is all.”

Cas makes a face, then squints in that adorable way that he does.

_Adorable? What?_

“Stay with me,” Cas says suddenly, and Dean is so caught off guard that he nearly drops the beer in his hand.

“Stay… huh?”

“Stay here, just for a while.”

It’s an odd request, but it’s not like Dean was going to sleep anyway.

“Why not,” he answers, and grabs a book off the top shelf that he’s been reading when Sam isn’t home to catch him. It may or may not be an old sci-fi novel. He puts his drink on one of the tables and plops down on the chair next to Cas, who smiles at him before turning back to his own book.

They sit in comfortable silence for almost an hour, the only sounds are of turning pages and a ticking clock on the wall and their breathing. They make small talk every time Dean verbally reacts to something in the story he’s reading, but mostly, they just…enjoy each other’s company.

Have they never done this before?

“Dean?”

“Yeah, Cas?”

“Would you say you were… _drawn_ here tonight?” Cas asks slowly.

Dean looks up. He isn’t sure what to say to that, or why Cas is asking. The angel is being weirder than usual.

“Here, like, to the library?"

Cas nods.

“Uh, I guess?”

“Oh,” Cas replies with a smirk. “Okay then.”

“ _Okay then?_ ” Dean repeats, “What’s that supposed to mean? You sure you okay, man?”

“Yes, Dean, I’m sure,” Cas says, closing the book in his hand and placing it on the table next to him. He grabs his coat and walks toward Dean, stopping in front of him and laying a hand on the side of his neck. He pauses for a second, smiles, then says, “Goodnight, Dean.”

And then, he’s walking out of the room, and Dean’s got a lump in his throat that doesn’t go away until he’s passing out an hour later.

///

The next morning, Dean decides that _whatever_ happened yesterday was a fluke. He’s fine, Cas is fine, everything is _normal._ He gets up, showers, brushes his teeth, and dresses, as per usual. He’s pulling on a flannel when there’s a knock at his door.

Grumbling, Dean walks over to open it, and freezes at the sight of Cas, wearing _sweats_ and one of _Dean’s_ old t-shirts, leaning against the door frame.

“Hey,” Cas says, and _has his voice always been that deep?_

“Uh, hi, Cas, um,” Dean stutters. He clears his throat, “What are you wearing?”

“ _Loungewear_ ,” Cas replies, finger quotes and all. “Can’t spar in my suit.”

Dean raises a brow, “Since when you do spar?”

“ _We,”_ Cas corrects, “Sam says exercise is important, and we should keep our fighting skills up. Sam’s been practicing with Jack, so I thought we could try it, too.”

“Yeah, because Jack is a baby half-angel. And Sam is a nerd.”

“But he’s not wrong. Maybe it will be fun? Please?”

Dean wants to tell Cas how ridiculous he sounds, but for some reason, he doesn’t think he can say no to the angel. He tries not to read too much into that.

Half an hour and two cups of coffee later, Dean finds himself knocked onto his ass for the third time in a row.

“Not fair,” he grunts from the padded floor of the gym, rolling over to push himself up, “You have angel powers.”

“I’m not using them, Dean. That would be cheating.” Cas responds matter-of-factly.

They’re going at each other with angel blades, but Cas keeps knocking Dean’s out of his hand. He goes to retrieve it, _again,_ and shrugs his flannel off of his shoulders, throwing it into a corner. He’s gotta redeem himself, this is just embarrassing.

“Well you’ve gotta be cheating somehow,” Dean jokes, “No way I lose three times in a row.”

Cas shrugs, readying himself to go again, “Maybe you’re just getting rusty.”

Dean squints at the other man. “Are you… baiting me?”

Cas smirks at him, “Maybe. Is it working?”

 _Oh?_ “Why don’t you come find out?”

Dean barely jumps out of the way as Cas lunges at him. Spurred on by the challenge, Dean actually holds his own for a while, meeting every attack with his own and dodging every blow. They’re both sweating by the time he finally manages to corner Cas, arm against his throat and blade at his stomach.

“Aha!” Dean shouts victoriously as Cas struggles to escape the hold, but with his back against the wall, he’s trapped. “Shouldn’t have left your core exposed, buddy.”

Cas huffs a tired laugh, looking at Dean through his lashes, then he says something the hunter doesn’t expect.

“I’m always exposed when I’m with you.”

“Wh…what?”

Dean is distracted for _maybe_ three seconds, four _tops_ , but Cas is quick, swipes the blade away from him and drops his body, then throws himself forward, and they both end up sprawled on the floor, Dean with the wind knocked out of him, and Cas’s blade against Dean neck.

“Alright, I yield, or whatever,” Dean wheezes, his body protesting against supporting the weight an entire angel, and when he opens his eyes, Cas is panting, and chuckling.

“What are you laughing about, asshole?” Dean coughs, trying his best to be bitter, but really, he had…fun.

Cas pulls himself off of Dean slightly, pulling the blade back and tucking it into the waistband of his pants. He shakes his head to get the hair out of his face, then leans down again, and whispers, “I win.”

Dean is frozen under Cas, hyperaware of his knee between his legs and the other next to his hips, Cas’s hands splayed on either side of his head, and Dean’s brain is currently short-circuiting from the _feelings_ he’s having, feelings he doesn’t want but can’t seem to get rid of, and Cas isn’t moving. Instead of getting off of him, Cas is _smirking_ again, and Dean is trying to figure out what the hell is happening when the doors to the gym open and Sam walks in.

Both men on the floor turn their heads to look at Sam, and Sam looks back at them, then stops in his tracks.

“Uh, should I…come back later?”

“No,” Dean scrambles to say.

“Yes,” Cas responds simultaneously.

They look at each other again, Dean’s eyebrows raised in question.

Cas grumbles then, rolling off of Dean and standing up.

“Sorry, I meant no, Dean and I have finished. I won.”

“He cheated!” Dean grunts, getting to his feet.

Cas rolls his eyes, “I did no such thing. He’s a sore loser.”

Sam laughs at that, “You’re telling me.”

“Hey!”

“I’m going to shower now,” Cas continues, ignoring Dean’s complaint. “See you both later.”

Once he’s gone, Sam gives Dean a look.

“Shut up, Sammy,” Dean tells him.

Sam throws up his hands, “I was just going to ask if you guys had a moment –.”

“Shut up!”

Sam is still laughing when Dean stomps out of the gym.

///

Dean’s eating a grilled cheese watching Scooby Doo on his laptop, feet propped up on the table, much to Sam’s disgust. Jack is watching with him, laughing when he _gets_ a joke, which is more often than before, so Dean counts it as a success. Sam sits across from them, reading lore for _fun,_ like the nerd he is.

Cas strolls in, sans trench coat or tie, just black slacks and a white button down with the sleeves rolled up to his elbows. Dean has to physically rip his eyes away. If Sam notices, he’s smart enough to keep his mouth shut.

“Hello, Cas,” Jack greets him.

“Hey, Jack,” Cas nods.

“Where you been, Cas?” Sam asks him.

“Shopping,” he replies.

Dean looks up again, “Since when do you shop?”

“I wanted to buy you something.”

Dean looks around awkwardly. “Uh, just me?”

“Yes.”

Sam snickers. Dean shoots him a glare.

“That’s very thoughtful,” Jack observes, “People buy things for people they care about, right?”

“That’s correct,” Cas nods, “I care very much about Dean.”

Dean almost chokes on his sandwich, and Sam looks _way_ too pleased about it.

“Alright, let’s go,” Dean is up and out of his chair, the rest of his sandwich abandoned on the table. He grabs Cas by the arm and leads him out of the room until they’re in the living area. He stops then, turns to look at Cas, and takes a deep breath.

“Cas,” he starts.

“Yes, Dean?”

Cas tilts his head, blue eyes boring into his own.

Dean closes his eyes, exhales, starts again.

“Cas, you don’t have to buy me things.”

“I know,” he says, “but I wanted to.”

Dean sighs, “Alright, what did you get me.”

Cas runs off to get whatever he bought from his room, and comes back with a wrapped present, bow and all. Dean blinks.

“Dude, what is this, Christmas?”

“No, but I didn’t want to wait,” he explains.

“That was a rheto – never mind. What is it?”

“Open it,” Cas urges him. He hands it over, and it’s _heavy._

“Yeesh, it weighs a ton,” Dean comments, sitting down on the couch to rip open the wrapping paper. He sees the front of it and pauses. “Wait, no way.” He tears the rest of the paper off, revealing the complete Led Zeppelin collection, on vinyl.

“They are your favorite, right?”

“Yeah!” Dean shouts excitedly. “Holy shit, Cas, where the hell did you find the entire collection?”

“On the internet,” he shrugs. “Bought it from some collector. I thought you’d enjoy it.”

Dean is speechless. He’s got a few records, sure, but the whole damn collection? It’s not something he ever needed, but now that he has it, he wonders why he didn’t get it himself ages ago. Somehow, though, getting it from Cas means so much more.

“You really didn’t have to do this,” Dean reiterates.

“But I’m glad I did,” Cas says, “I wanted to make you happy.”

“My happiness probably cost you a pretty penny,” Dean jokes.

“You’re worth it.”

Dean blinks up at Cas, who is looking at him in a way that makes him want to bolt, but at the same time, he feels so warm and cared for and _safe_ , and it’s so terrifyingly comfortable, he has to look away.

“Thanks, Cas,” he mutters, sliding his hand over the collection, “I love it.”

///

The next week, Dean thinks maybe Cas’s odd behavior around him will stop, and things will go back to normal.

It doesn’t.

They catch a case. It’s only a state away, and the four of them drive there. Sam and Jack go interview the victim’s friends and neighbors, while Dean and Cas hit up the local police station to see what they know. The detective in charge is an older woman, mouthy, and has zero filter.

“You know, I usually hate having the FBI in my town,” she says, smacking her gum loudly as she flips through files on the desk, “But you’re a pretty one, so I’ll play nice.”

“He is pretty, isn’t he?” Cas agrees, “I don’t think he realizes it.”

Dean almost drops his fake badge.

“His eyes are especially impressive. And his freckles remind me of all the galaxy’s stars.”

“See, your partner gets it. Probably why you put up with his arrogant ass, huh? I know the type.”

“Whoa whoa whoa, I’m not arrogant,” Dean argues.

“You can be, sometimes,” Cas corrects, and Dean glares at him.

“Dude.”

“Don’t worry, I don’t hold it against you.” 

“Bet you hold something else against him, hmm?” The detective winks at them, and before Dean can process what just happened, she’s handing them the files they need and sending them on their way. Dean can’t get out of there fast enough.

“What the hell was that?” Dean asks once they’re in the car.

Cas looks at him like he’s crazy, “What was what?”

“Dude, you called me _pretty._ ”

“Oh, that,” Cas shrugs, “The detective noticed your beauty, I simply thought you should know that I agree. You _are_ very beautiful, Dean. Every part of you.”

Dean shakes his head, but then Cas reaches out, puts his hand on Dean’s where it sits on the gear shift.

“Dean, I mean it.”

Dean knows. Somehow, Dean knows he means it, but he doesn’t have a response for that, besides the feeling of his heart in his throat. So, he looks away, and drives.

///

Turns out, they’re hunting shapeshifters who shift into rich townspeople, throw extravagant parties to lure other people in, and snatch up whomever they have a grudge against. They aren’t sure why, but it ends tonight.

They get into the party pretty easily, dressed up like rich assholes. Sam and Jack sneak upstairs to look for anyone that may already be a hostage to the shifters, while Dean and Cas stand watch at the bar, silver in hand to test anyone that gets close. Sam was able to find them some earpieces so they can communicate even if they split up. Dean is giddy about the new tech, but no one needs to know that.

“Second floor is clear,” Sam’s voice comes through the sharply in Dean’s left ear. He looks at Cas, who is making small talk a few yards away. He shakes his head, no sign of the shifter yet.

“I’ll check the third floor,” Jack chimes in.

“I’ll head to the basement,” Sam adds. “Any news on the main floor?”

“Expensive drinks and cheap people,” Dean comments. “No action yet, we’ll keep looking.”

Dean sips his whiskey slowly, trying his best to blend in, when the earpiece crackles again.

“Hey, handsome.”

Dean all but spits out his drink on the lady next to him, apologizing when she eyes him suspiciously after his coughing fit. He recovers, finally, and looks around the room for the person to blame. He spies Cas directly across from him, standing lazily against the wall like he’s already drunk, which isn’t possible.

“What the _hell,_ Cas!” Dean whispers.

“I thought that one may be too much. How about Freckles?”

Sam laughs through the earpiece.

“Sam, shush. Cas, what are you talking about?”

“I feel this case needs code names, don’t you think? I was thinking of one for you.”

“Oh, I want one!” Jack adds, “How about, Nephilim?”

“That’s a bit on the nose there, Jack,” Sam states.

“We aren’t doing code names, Sasquatch!” Dean protests.

“What would I be?” Cas asks.

“Nothing, you’re nothing! No code names!” Dean all but shouts.

Cas visibly frowns from across the room. _Shit._

“Wait, Cas, I didn’t mean –.”

“It’s okay, Dean. You’re right. We should focus on the case. I’ll go search out back.”

Cas walks through the crowd and slips out the back door, avoiding Dean’s eyes.

“I think you upset him,” Sam mutters.

“Shut _up,_ Sam,” Dean grunts, making his way to the back door and following Cas outside. The grass outside is wet and Dean wishes he were wearing his boots and jeans, not this rented tux. He searches everywhere but can’t find the damn angel.

“Great,” Dean huffs, making his way back inside. “He’s gone.”

“He’s probably tired of you ignoring his feelings,” Sam’s voice crackles.

“His feelings?”

“Dean, the guy has been flirting with you for a week, and you’ve barely noticed.”

Dean lets that sit with him for a moment. Cas was _flirting_ this whole time _._ Dean’s felt _something_ when they’ve interacted lately, but thought it was just a combination of their profound bond and Cas just being weird. He also has buried his own feelings down so deep he’s almost convinced himself that Cas could never feel that way about him. So, maybe he did know, after all.

“So, I was just supposed to assume Cas had feelings for me?!”

“You’re an idiot sometimes, you know that?” Sam sighs. “Oh, and I found the hostages in the basement. They were a little beat up, but alive. I’ll get them out.”

“Alright. Jack, you okay?”

“Yes, there’s evidence that a shifter definitely shed here recently. They must be in the crowd downstairs.”

“You stay up there in case the shifter comes back. I’m headed to you.”

“Okay. Also, what is flirting?”

Sam laughs again. Dean rolls his eyes.

“We’ll explain later, Jack.”

///

They catch the shifters eventually. All things considered, it’s an easy kill.

They get back to the motel, and Dean tries not to make his disappointment too obvious when Cas isn’t there waiting for them. He’s not there the next day when they drive back to the bunker. When they arrive home, Dean checks Cas’s room, and sighs when he’s not there either.

“Fuck it. Grow up, Winchester.”

He steps into the room, sits on the edge of the bed, bows his head, and prays.

“Cas, are you there?” he starts. “I hope you can hear me. Look, man, I’m sorry for taking so long to figure out why you’ve been weird all week. You can thank Sam for spelling it out for me. I guess I just… I don’t know how to accept your affection?” Dean shakes his head. “Which is a shit excuse, I know, but… what we have, Cas, it’s special, I know that. I know you have feelings for me, it’s obvious now, and I guess I’m just scared. No, I know I’m scared. I’m terrified, really. Because…” Dean wrings his hands together. He’s not sure why he’s nervous. He’s known about his feelings for years; he’s just never said them out loud. Never thought the angel could possibly feel the same way. But now…

“I think I feel the same way about you, and I don’t know what to do about it. This isn’t… I’m not good at this kind of thing. If we… I don’t want to hurt you, Cas. My worst fear is that I’ll hurt you and lose you forever. I don’t think I could stand to lose you. Not again.”

It’s then that he hears it, the flap of wings. He opens his eyes and Cas is standing in front of him. Dean practically jumps to his feet.

“Cas,” he breathes, “You came back.”

“I will always come when you call,” he says, like it’s the simplest thing in the world. “Always.”

Dean pulls the angel into a hug, wrapping his arms around his shoulders. Cas returns the embrace, his arms settling tightly around Dean’s waist. They stay that way for a long moment, and Dean finds himself not wanting to let go.

“I’m sorry I’m an idiot,” he says against Cas’s neck.

“You’re not an idiot,” Cas says into his hair. “I’m scared, too.”

Dean pulls back enough to look Cas in the face. “So, what’s with the boldness all of a sudden?”

Cas chuckles a little, shaking his head. Dean raises a brow.

“Rowena, um, she uh, performed a spell –.”

“That _witch –.”_

“— to make me braver with my affection.”

Dean’s mouth snaps shut. _Wait, what?_

“Hold on, you had Rowena give you some sort of love magic so that you had the balls to flirt with me?”

Cas rolls his eyes, “Well, when you put it _that_ way, it sounds ridiculous.”

Dean can’t help but laugh, “Because it is, Cas.”

Cas frowns, but Dean shakes his head, moves his hands to Cas’s face.

“I mean, it’s the most ridiculous thing anyone has ever done for me. You must have it bad.”

Cas nods, “The depth of my feelings for you is… exponential to what I’ve ever felt for another person, angel or human. I could drown in it. Part of me wants to. I just didn’t know how to tell you.”

“Well, I know now,” Dean whispers, thumbs caressing the angel’s cheeks, wiping away the tears that have suddenly appeared there. He looks into Cas’s eyes. “I know, and I feel the same way.” 

“ _Dean._ ”

Dean feels that pull again, like a compass always leading him home, and he follows it. He kisses Cas, and it feels so _right_ he thinks his heart might explode. Kissing Cas is unlike anything Dean could have imagined. Better than fireworks on the Fourth of July, better than a full eight hours of sleep, better than the sun on your face first thing in the morning, better than pie, better than driving Baby – kissing Cas is something more amazing all together, and Dean can’t believe he denied himself this pleasure for _so damn long._

Because, holy _hell,_ the angel can _kiss._

Dean isn’t sure how much time has passed when they finally break apart, but they’re both panting when the do. Cas is looking at him like he’s the most precious thing in the world, and Dean’s first instinct is to shy away, but Cas doesn’t let him. He places a warm hand on his neck and pulls Dean’s chin back up with his thumb.

“Let me look at you,” Cas says gently.

Dean’s got honest-to-God butterflies. _Butterflies._ He’s so gone.

“ _Caaas_ , come on,” Dean whines, and _Jesus Christ,_ one kiss and he’s reduced to a little girl.

“You’re so beautiful, Dean,” Cas continues, their faces only inches apart, “I hope you believe me now when I say it.”

“I do,” Dean replies, surprised to find that he’s practically breathless. Being so close and not kissing is sensory overload. Dean feels Cas _everywhere,_ it’s like he’s on fire. How did he survive so long around Cas and _not know,_ how did he not feel this before?

“Thank you,” he hears himself saying, “Thank you for not giving up on me.”

“I could never do such a thing,” Cas answers, resolute, like it’s always been true.

“I don’t want to lose you.”

“You won’t.”

Dean breathes for the first time in what feels like hours. He won’t lose Cas. Cas won’t lose him. That’s all he’s wanted for so long, isn’t it?

“I… I –.” There are three words sitting heavy on his tongue. He wants to say them, but the weight of them feels like too much right now. He looks at Cas, tightens his grip on his trench coat. Shit, he’s crying too, isn’t he?

“I know,” Cas tells him, and kisses him again. And with that kiss, he spells out exactly how he feels. Dean’s not sure how, but he swears he can hear him, clear as a bell.

_I love you, too._


End file.
